Long term rentals Castellina In Chianti | Holiday Lettings

Close

View larger map

Also consider

Europe Holidays
431300 properties
Italy Holidays
103659 properties
Tuscany Holidays
25275 properties
Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties

Castellina In Chianti

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

153 Holiday homes

(2)  

30

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £119 / night

£470 - £709 / week

Book View

from £119 / night

(5) Excellent 

48

Province of Siena / Castellina In Chianti

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 150 km
  • Child friendly
  • Private garden

 …see more

from £103 / night

£488 - £582 / week

Book View

from £103 / night

20

Province of Siena / Castellina In Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

 …see more

from £107 / night

£748 / week

Book View

from £107 / night

(2) Very Good 

100

Castellina In Chianti holiday villa rental

Province of Siena / Castellina In Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This grand house, with 5 bedrooms and 5 bathrooms can host 10 people, so it is ideal for large families. Located in Tuscany Italy, this house offers a swimming Pool, an internet Connection .  …see more

from £337 / night

£1965 - £2943 / week

Enquire View

from £337 / night

24

Holiday villa letting

Province of Siena / Castellina In Chianti

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Everything about this property is classically Tuscan. If you dream of typical Tuscany as breathtaking panoramas, misty hills covered in precision lines of vineyards, olive groves, gravel roads and driveways shadily lined with pointy cypress trees, and grand villas with  …see more

from £568 / night

£3975 / week

Enquire View

from £568 / night

8

Holiday villa with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
Il Torrino is a wonderful 4 bedroom villa set within a small and perfectly kept Tuscan medieval village and situated atop a hill with stunning views over the Chianti vineyards. Once a Medieval watch tower, the property oozes character and charm, but has been completely  …see more

from £178 / night

£1240 - £2308 / week

Book View

from £178 / night

24

Holiday farmhouse with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
www.ilcellese.it  …see more

Pricing unknown

Book View

Pricing unknown

(1) Excellent 

24

Villa rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Villa Patrignone has 7 large double bedrooms, each with private bathroom, a cavernous kitchen-dining room with large fireplace, and a lovely living room, with high vaulted ceilings, comfortable sofas and a library. The house was built sometime in the 1500s and still has  …see more

from £387 / night

£2318 - £4003 / week

Book View

from £387 / night

100

Holiday villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in Tuscany Italy, this gorgeous accommodation is the perfect place for your holidays. The accommodation features: a swimming Pool, air Conditioning .  …see more

from £414 / night

£2894 - £4207 / week

Enquire View

from £414 / night

(2) Excellent 

22

Province of Siena / Castellina In Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly

 …see more

from £37 / night

£257 - £385 / week

Book View

from £37 / night

13

Holiday cottage with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Private garden
Beautiful cottage with private garden and access to pool with amazing sunset views  …see more

from £129 / night

£770 / week

Book View

from £129 / night

16

Province of Siena / Castellina In Chianti

9 16 Min stay varies

  • 9 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

Book View

Pricing unknown

18

Holiday farmhouse in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
CHIANTI , SWIMMING POOL , VIEW , COOKING CLASS, AGRITURISMO , NATURE , RELAX , LANDSCAPE , WINE  …see more

Pricing unknown

Book View

Pricing unknown

16

Holiday castle with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Relais chianti, luxury apartment chianti, hamlet chianti, medieval village, infinity swimming pool ,outdoor dining area , barbecue grill.  …see more

from £134 / night

£938 - £1300 / week

Enquire View

from £134 / night

100

Holiday villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
elegant house sleeps 16 people, so it is perfect for a large group of friends and is located in Tuscany Italy. This property is ideal if you seek a relaxing holiday. The villa features: a swimming Pool, air Conditioning, an internet Connection .  …see more

from £388 / night

£2716 - £2724 / week

Enquire View

from £388 / night

13

Home rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Luxury interior designed 2 bedroom house in stunning position in Chianti countryside with a private garden (half acre) and 2 terccaces. Shared swimming pool and tennis courts within a medieval village setting. 12km from Castellina in Chianti, 7km from Poggibonsi. Stunn  …see more

from £83 / night

£575 / week

Book View

from £83 / night

16

Castellina In Chianti holiday villa rental

Province of Siena / Castellina In Chianti

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This beautiful, detached stone farmhouse, situated near Castellina in Chianti, was restored in 1995. Surrounded by ample private grounds, it sits in a panoramic position and is reached by its own driveway  …see more

from £527 / night

£2105 - £3440 / week

Enquire View

from £527 / night

14

Holiday farmhouse rental

Province of Siena / Castellina In Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
WINE , CHIANTI CLASSICO , CHIANTI , COOKING CLASS , VIEWS , LANDSCAPE  …see more

Pricing unknown

Book View

Pricing unknown

23

Holiday farmhouse rental

Province of Siena / Castellina In Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
CHIANTI , WINE , COOKING CLASS , AGRITURISMO , LANDSCAPE , VIEW  …see more

Pricing unknown

Book View

Pricing unknown

(1) Very Good 

24

Holiday apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Four rooms, 90 sqm, fully equipped kitchen and living room, 3 double bedrooms (one with high window). Inside, each bedroom has TV and bathroom with shower (total 3 baths).  …see more

from £142 / night

£988 - £1167 / week

Book View

from £142 / night

(3) Very Good 

24

Province of Siena / Castellina In Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly

 …see more

from £196 / night

£1371 / week

Book View

from £196 / night

16

Province of Siena / Castellina In Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £197 / night

£1197 / week

Book View

from £197 / night

14

Province of Siena / Castellina In Chianti

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly

 …see more

from £42 / night

£273 - £483 / week

Book View

from £42 / night

13

Holiday farmhouse in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
CHIANTI , TOSCANA , AGRITURISMO , WINE , COOKING CLASS , LANDSCAPE , VIEW , SWIMMING POOL  …see more

Pricing unknown

Book View

Pricing unknown

(2) Excellent 

20

Holiday farmhouse in Castellina In Chianti

Province of Siena / Castellina In Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
“An excellent slice of Tuscan beauty” The week spent at Casa del Fico was most delightful. A perfect location atop a hill with 360 degree views of Tuscany reminiscent of any da Vinci painting. Ideally located to either explore the local region or just  …see more

from £183 / night

£1275 - £2150 / week

Book View

from £183 / night

14

Castellina In Chianti holiday apartment rental

Province of Siena / Castellina In Chianti

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Le Stalle is a lovely 2-bedroom apartment situated on the ground floor of Podere Patrignone, a 15th century farmhouse in the heart of Chianti, surrounded on all sides by olives, vines, hills and forest. It has a kitchen, dining area, outside porch and use of the pool.  …see more

from £183 / night

£1094 - £1183 / week

Book View

from £183 / night

(3) Excellent 

24

Castellina In Chianti holiday apartment rental

Province of Siena / Castellina In Chianti

2 8 4 nights min

  • 2 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 90 km
  • Child friendly
  • Private garden
Large, elegant, comfortable apartment in incomparable surroundings. Peaceful and relaxing with spectacular scenery. 3 km from Castellina in Chianti with its medieval town centre, shops, bars, restaurants. 22 km from Siena., 37km from Florence. No neighbours or noise.Pe  …see more

from £107 / night

£748 / week

Book View

from £107 / night

14

Holiday farmhouse letting

Province of Siena / Castellina In Chianti

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
WINE , CHIANTI , DOCG, VIEW , LANDSCAPE , AGRITURISMO  …see more

Pricing unknown

Book View

Pricing unknown

17

Castellina In Chianti holiday farmhouse rental

Province of Siena / Castellina In Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in Castellina In Chianti with 3 bedrooms sleeps 6  …see more

from £112 / night

£659 - £1105 / week

Enquire View

from £112 / night

15

Apartment rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
Bed and bathroom linen and kitchen teatowels, hairdryer, water, gas and electric consumption, central heating, final cleaning, pool use, car park, ping pong, barbecues, washing machine for common use, wi-fi in common area, 6 bikes for adults, on request iron and ironing  …see more

from £60 / night

£419 - £509 / week

Book View

from £60 / night

100

Holiday apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
Carming apartments in a medieval hamlet in heart of Tuscany, all the apartments have been carefully restored, swimming pool  …see more

from £98 / night

£683 - £1131 / week

Enquire View

from £98 / night

36

Province of Siena / Castellina In Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £110 / night

£770 - £1112 / week

Enquire View

from £110 / night

18

Castellina In Chianti holiday farmhouse rental

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

from £112 / night

£659 - £1105 / week

Enquire View

from £112 / night

25

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £103 / night

£684 - £941 / week

Book View

from £103 / night

18

Castellina In Chianti holiday farmhouse rental

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

from £112 / night

£659 - £1105 / week

Enquire View

from £112 / night

100

Holiday villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
This extraordinary villa welcomes up to 12 people in its ample common areas and bedrooms, and it has a wonderful garden and swimming pool. It is ideal for large families or groups of friends.  …see more

Pricing unknown

Enquire View

Pricing unknown

100

Holiday apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
Carming apartments in a medieval hamlet in heart of Tuscany, all the apartments have been carefully restored, swimming pool  …see more

from £159 / night

£1107 - £1825 / week

Enquire View

from £159 / night

100

Holiday apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
Carming apartments in a medieval hamlet in heart of Tuscany, all the apartments have been carefully restored, swimming pool  …see more

from £104 / night

£724 - £1191 / week

Enquire View

from £104 / night

(2) Very Good 

23

Apartment rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in Tregole with 2 bedrooms sleeps 4  …see more

from £66 / night

£385 - £642 / week

Enquire View

from £66 / night

(4) Very Good 

28

Province of Siena / Castellina In Chianti

5 15 Min stay varies

  • 5 bedrooms
  • Sleeps 15
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £184 / night

£1282 - £3820 / week

Book View

from £184 / night

Top Destination reviews

Farm holidays in Chianti
A Christams dream

This year my husband and I decided to spend Christmas on our own, in the Chianti countryside. La Capanna delle Cozzole is just the perfect location: very quiet, romantic and private location. In the village you can find top quality food, wine and d … see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page